ArticleWhen Is a Trifluoromethyl Group More Lipophilic than a Methyl Group? Partition Coefficients and Selected Chemical Shifts of Aliphatic Alcohols and Trifluoroalcohols
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2014, Coordination Chemistry ReviewsDiastereospecific fluorination of substituted azepanes
2013, TetrahedronCitation Excerpt :The 1,2-trans-benzyloxyazido substitution motif in 7 can be easily reduced to 1,2-trans-hydroxylamino motif found in many bioactive natural products.15 The 3-aminoazepane motif is also seen in antitumor cis-platin analogs16 and somatostatin mimics.17 Therefore fluorinated azepane building blocks from 7 will have wide utility in diversity-oriented synthesis of fluorinated bioactive leads.
Obtention of enantiomerically pure 5,5,5-trifluoro-l-isoleucine and 5,5,5-trifluoro-l-alloisoleucine
2013, Journal of Fluorine ChemistryCitation Excerpt :Unfortunately, 8 is not commercially available and must be synthesized. The procedure applied by Müller and Tirrell to obtain this intermediate employs direct electrolysis of methallyl cyanide and trifluoroacetic acid in presence of sodium acetate [10,13,15]. This procedure is decidedly inconvenient for most preparative applications on a small scale and normally produces a highly complex mixture of several products besides the desired one.
Trifluoromethylation of aryl and heteroaryl halides
2011, TetrahedronCitation Excerpt :While preparing novel derivatives with potential indications toward orexin receptor antagonists, Aissaoui reported trifluoromethylation of a Boc-protected dihydroimidazopyrazine iodide (entry 8).20 Trifluoromethylation of a highly substituted 5-bromopyrimidine was carried out by Coteron and co-workers using MFSDA–CuI to afford novel heteroaryl nitrile derivatives as cysteine protease inhibitors (entry 9).21 The preparation of a 3-trifluoromethyl-2H-indazole, bearing a para-methoxyphenyl (PMP) protecting group, was reported by the Katzenellenbogen group where they treated the corresponding bromide with MFSDA (5 equiv) and CuI (1 equiv) in DMF at 80 °C for 2 h.